Regioselective catalytic alkylation of N-heterocycles in continuous flow

Tamás Sipőcz; László Lengyel; Gellért Sipos; László Kocsis; György Dormán; Richard V. Jones; Ferenc Darvas

doi:10.1556/1846.2015.00030

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Journal of Flow Chemistry

Volume/Issue:: Volume 6: Issue 2

Regioselective catalytic alkylation of N-heterocycles in continuous flow

Authors:

Tamás Sipőcz

Tamás Sipőcz ThalesNano Inc.,, Záhony utca 7, DB building, 1031 Budapest, Hungary

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László Lengyel

László Lengyel Innostudio Inc.,, Záhony utca 7, DB building, 1031 Budapest, Hungary

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Gellért Sipos

Gellért Sipos ThalesNano Inc.,, Záhony utca 7, DB building, 1031 Budapest, Hungary

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László Kocsis

László Kocsis ThalesNano Inc.,, Záhony utca 7, DB building, 1031 Budapest, Hungary

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laszlo.kocsis@thalesnano.com

György Dormán

György Dormán ThalesNano Inc.,, Záhony utca 7, DB building, 1031 Budapest, Hungary

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Richard V. Jones

Richard V. Jones ThalesNano Inc.,, Záhony utca 7, DB building, 1031 Budapest, Hungary

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, and

Ferenc Darvas

Ferenc Darvas ThalesNano Inc.,, Záhony utca 7, DB building, 1031 Budapest, Hungary

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Pages:: 117–122

Online Publication Date:: Jun 2016

Publication Date:: 01 Jun 2016

Article Category:: Research Article

DOI:: https://doi.org/10.1556/1846.2015.00030

Keywords:: flow chemistry; C–H activation; catalytic alkylation; nickel catalysis

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A novel method for C–H functionalization of heteroaromatic rings by using continuous-flow reactors is reported. Direct alkylation reactions were investigated under heterogeneous catalytic conditions using simple transition metal catalysts at elevated temperature and pressure. As a model reaction, the alkylation of indole was attempted using cheap Raney® Nickel catalyst. Alcohols served both as alkylating agent and as reaction media. The targeted 3-alkyl-indoles were obtained in moderate to good yield with reasonable selectivity. Transient protection on the N-atom increased the selectivity up to 80%. The scope and limitations were also investigated. In summary, direct alkylation with alcohols represents a rapid (residence time of <1 min) and traceless process with high atom economy (88–92%, in those cases where transient protection was not applied).

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Journal of Flow Chemistry A Journal of the Flow Chemistry Society

Print ISSN:: 2062-249X

Online ISSN:: 2063-0212

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Journal of Flow Chemistry
Language	English
Size	A4
Year of Foundation	2011
Volumes per Year	1
Issues per Year	4
Founder	Áramlásos Kémiai Tudományos Társaság
Founder's Address	H-1031 Budapest, Hungary Záhony utca 7.
Publisher	Akadémiai Kiadó Springer Nature Switzerland AG
Publisher's Address	H-1117 Budapest, Hungary 1516 Budapest, PO Box 245. CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible Publisher	Chief Executive Officer, Akadémiai Kiadó
ISSN	2062-249X (Print)
ISSN	2063-0212 (Online)